Effect of β-Cyclodextrin on the Hydrolysis of Trifluoroacetate Esters
- 12 May 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (12) , 4399-4404
- https://doi.org/10.1021/jo001691k
Abstract
The hydrolysis of p-F, p-Cl, and m-Cl phenyl trifluoracetates was studied in the presence of β-cyclodextrin (β-CD). The reactions are inhibited by β-CD at pH 6 while they are catalyzed in alkaline solution. MM3 calculations reproduce some of the experimental results. The substrates form inclusion complexes with β-CD which are of similar stability as those of the corresponding acetates; however, the association of the transition state is less favorable in these reactions than in those of the acetates, and consequently less stronger catalysis is observed.Keywords
This publication has 32 references indexed in Scilit:
- On the Mechanism of Ester Hydrolysis: Trifluoroacetate DerivativesThe Journal of Organic Chemistry, 1999
- Determination of the Inclusion Geometry for the β-Cyclodextrin/Benzoic Acid Complex by NMR and Molecular ModelingThe Journal of Organic Chemistry, 1996
- Computer Modeling of Phenyl Acetate Hydrolysis in Water and in Reaction with .beta.-Cyclodextrin: Molecular Orbital Calculations with the Semiempirical AM1 Method and the Langevin Dipole Solvent ModelThe Journal of Physical Chemistry, 1995
- Semianalytical treatment of solvation for molecular mechanics and dynamicsJournal of the American Chemical Society, 1990
- Origin of rate accelerations in an enzyme model: the p-nitrophenyl ester syndromeJournal of the American Chemical Society, 1987
- Infrared spectra of trifluoroacetate estersJournal of Fluorine Chemistry, 1971
- The mechanism of the cycloamylose-accelerated cleavage of phenyl estersJournal of the American Chemical Society, 1967
- Acceleration of phenyl ester cleavage by cycloamyloses. A model for enzymic specificityJournal of the American Chemical Society, 1967
- Transition State Characterization for Catalyzed ReactionsJournal of the American Chemical Society, 1963
- Aromatic Esters of Fluorocarbon AcidsJournal of the American Chemical Society, 1953